Investigation of α-Thioglycoside Donors: Reactivity Studies toward Configuration-Controlled Orthogonal Activation in One-Pot Systems

• DOI: 10.1021/acs.orglett.6b01572
• Publication Date: 2016-07-11T18:36:20Z
• Authors: Raymond Smith; Helge Müller-Bunz; Xiangming Zhu
• Keywords: Reactivity; Moiety; Chemoselectivity; Oligosaccharide

The influence of anomeric configuration upon thioglycoside donors remains relatively unexplored. Utilizing methodology developed for the stereoselective and high-yielding synthesis α-glycosyl thiols, a series α-thioglycosides were synthesized, their reactivity was compared to that β-counterparts. highly selective activation observed pairs containing 2-O-acyl moiety additional findings are reported. Application pair "superarmed" thioglycosides one-pot oligosaccharide system is also described, in which selectivity result configuration-based orthogonal activation.